Red glasses are the one color choice in drinkware that actually makes your table look finished instead of just set, and I say that as someone who spent a year drinking water out of mismatched jars before admitting it. Clear glass is fine, but it disappears. Red does something on a table that nothing else does, it gives you a focal point without you having to try.
The shade matters more than you'd expect walking into it. A true, slightly deep red, the kind that leans toward wine rather than cherry, sits next to almost any dish towel, placemat or wood tone you already own. Bright cherry red or anything with an orange cast gets fussy fast and starts picking fights with your other colors. Go for red with a little weight to it, maybe a touch of amber or smoke in the glass itself, and you'll never stand there wondering if it matches. On sizing, measure your cabinet shelf height before you fall for a tall tumbler or a stemmed glass, because I lost an entire set of great looking red tumblers to a shelf that was an inch too short, and they lived in a box in the basement for four months before we got around to swapping the shelving. For a table, stick to a size that holds a real pour, something in the 12 to 16 ounce range for everyday glasses, and don't buy a dozen of anything until you know you like living with the color at all.
Start with a short set, four is plenty, in a simple tumbler shape rather than anything stemmed or etched, since a plain shape wears the color better and chips less at the rim over time. I went stemware first in our place and regretted it within a month, two broke in the dishwasher and I was down to a lonely pair for date nights.
Where red glasses get tricky is next to a lot of other saturated color already happening on the table, a red tablecloth, an orange centerpiece, patterned dishes with their own loud thing going on. In those rooms, let the glasses be the only color statement and keep everything else neutral, or skip them for that specific setting and save them for a simpler table. They also don't love being the only red note in an otherwise cool, gray, very modern kitchen, they can read like a random accent rather than a choice. After two years of regular use in our house, including one memorable Thanksgiving where my mother in law knocked one clean off the table onto the hardwood, ours are all still intact and have gone through a full move without a single casualty.
Buy the simple shape in the deep shade, and skip anything delicate you'll be afraid to actually use.
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